The tips collected at Kerry Wood’s charity event at Harry Caray’s Tavern at Navy Pier Friday went straight to the Wood Family Foundation, which might explain why the Cubs and Bears players working the “Woody’s Winter Warm-up” benefit seemed determined to earn gratuity by any means necessary.

The Cubs’ Randy Wells served drinks behind the bar and at one point allowed a middle-aged woman to stuff a $5 bill down the front of his collar. Former Bear Otis Wilson also got behind the bar but seemed to earn his biggest tips when he allowed guests to try on his Super Bowl ring from the triumphant 1985 team.

Cubs President of Baseball Operations Theo Epstein didn’t pour any drinks, but he seemed to pose for as many photos with guests as anyone else. He also showed off his guitar skills when he joined “Hey There Delilah” band Plain White T’s on stage to perform Neil Young’s “Rockin’ in the Free World.” Wells opted to play Tom Petty’s “Free Fallin’” with Plain White T’s.

The experience was likely a thrill for Plain White T’s lead singer and Elmhurst resident Tom Higgenson.

“My Dad would have the (Cubs) game on in the house every day in the summer,” Higgenson told me, adding that he is raising his son as a Cubs fan as well. “We already got him his first little Cubs hat. He’s already on his way.”

Also in attendance was former The Academy Is … frontman William Beckett, who performed earlier in the night, the Cubs’ Ryan Dempster, who hosted his own charity event for his Dempster Family Foundation the night before at D’Agostino’s in Wrigleyville, and the Bears’ Israel Idonije, who poured wine for guests.

The star of the evening, of course, was Wood. The 34-year-old pitcher has been a fan favorite ever since he made his Cubs debut in 1998, and it showed in the turnout Friday (about 400 guests were on hand for the benefit, which raised more than $80,000 for Wood’s children-focused charity). It appeared Wood’s future with the Cubs was in jeapordy in recent months, but fans officially received word at Friday’s Cubs Convention that he would be brought back for another season.

Did Wood ask Epstein if he could break the news himself at his charity event?

“No,” Wood told me. “I was just trying to get a job.”

The guests at Harry Caray’s were clearly excited about that day’s news and told Wood so throughout the night. When Wood was behind the bar serving drinks, one nearby fan used the opportunity to congratulate him on the new contract.

“Thank you, thank you,” Wood said before looking into the crowd and yelling, “Anybody need a drink?”

Before making the final media rounds to promote his “Woody’s Winter Warm-Up” benefit, the Cubs’ Kerry Wood stood in the waiting area of the posh 316 Club Barber Spa last week — where he would receive a haircut and shave — and gave me a reality check on his famous 20-strikeout performance. The 34-year-old...

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